


The Upper Hand

by MightyMidget



Category: Supernatural
Genre: Additional Warnings Apply, Anal Fingering, Anal Sex, Bondage, Castiel in the Bunker, Collars, Crossroads Deals & Demons, Crowley Being Crowley, Dark Past, Demon Dean, Demon Dean Winchester, Demon Sex, Dom/sub, Domestic Violence, Emotional Hurt, Emotional/Psychological Abuse, Evil Dean Winchester, Grace Sharing, Hand Jobs, Heavy Angst, Hell Torture, Hell Trauma, Hurt Castiel, Hurt Sam Winchester, I need a shower, Kidnapping, Loss of Virginity, M/M, Mark of Cain, Master Dean, Master/Pet, Master/Slave, Men of Letters Bunker, Mind Control, Mind Manipulation, Name-Calling, Non-Consensual Touching, Non-Consensual Violence, Non-Consensual Voyeurism, Other Additional Tags to Be Added, Past Abuse, Past Rape/Non-con, Past Sexual Abuse, Past Torture, Pet Castiel, Pet Sam, Powerlessness, Proceed with caution, Rape, Rape/Non-con Elements, Season/Series 10, Sexual Slavery, Sexual Violence, Slave Castiel, Slave Sam, Slavery, Slurs, Threats of Rape/Non-Con, Threats of Violence, Voyeur Dean, Voyeurism, What Have I Done
Language: English
Status: Completed
Published: 2015-09-29
Updated: 2015-10-28
Packaged: 2018-04-23 23:03:24
Rating: Explicit
Warnings: Rape/Non-Con
Chapters: 6
Words: 18,341
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/4895689
Author URL: https://archiveofourown.org/users/MightyMidget/pseuds/MightyMidget
Summary: <blockquote class="userstuff">
              <p>After bringing Dean back to the Bunker in the hopes of curing him, Dean gets loose and now its time for Sam and Castiel to pay the price for their foolishness.</p>
            </blockquote>





	1. Chapter 1

**Author's Note:**

> THIS WORK IS INSPIRED BY THE ARTWORK IN THE LINK BELOW!
> 
> http://vandlp1088.livejournal.com/4656.html
> 
> MAJOR THANKS TO THE LADIES AT WINCEST/J2 ON FACEBOOK FOR BELIEVING IN ME!

Bringing the Demon Dean back to the Bunker was the worst mistake Sam had ever made, and now as he sat on the floor of the Dungeon with his wrists cuffed to the wall above his head he  realised that there was nothing left of his Brother hidden away inside this black eyed dick.  
  
"Oh come on now Sammy, don't pout! It ain't that bad!" The Demon spoke with his Brothers voice.    
  
"Don't call me Sammy!" Sam growled but that only served to make the Demon laugh.  
  
"Feisty, I like that. I always did like a little fight in them..." The Demon said, tongue peeking out to wet his lips as his eyes raked over the Hunters body, and suddenly Sam was getting worried.  
  
"What the Hell are you talking about?!" Sam barked, trying to sound tougher than he felt but he could tell by the glint in those black eyes that the Demon could see right through him.  
  
"Now, Sammy! You really think I got you down here all trussed up just so I can stand here looking at you?" The Demon said as it slowly sauntered up to Sam, smirking when the realisation hit Sam like a punch to the face. "No. I am gonna have some real fun with you, little brother." Sam started to jerk harshly against the chains holding him in place but it didn't stop the demon from reaching out and slowly beginning to pop the buttons of his shirt open, one by one, working to expose the man's chest.  
  
"Dean please I know you are still in there somewhere! Please stop this we can work this out okay?" Sam babbled, voice becoming almost frantic as the Demon finished with his shirt, leaving it hanging open, and reached for his pants. "We can fix this!"  
  
"I told you already, Sam! It can't be fixed! There is nothing to fix! I sm not broken!!" The Demon hissed, putting his face in Sam's and glaring at him as he ripped open the mans jeans. "I am not broken, Sammy...but soon enough, you will be..."A frightened whimper escaped Sam's mouth as the Demon closed in on him,lips hovering only inches from Sam's when a sudden noise came from upstairs...  
  
It sounded like someone walking around and Dean was about to lose it when a voice called out to them.  
  
"Sam? Dean?..." Castiel was calling out as he searched for his friends in the Bunker above their heads. Sam opened his mouth to scream for help but the Demon silenced him with a flick on his wrist, turning to smirk at him.  
  
"Just in time...You ready to meet your new play mate, Sammy?" The Demon asked but he didn't wait for an answer, instead he turned away and made his way to the door, pulling his blade from his belt and heading upstairs, leaving the poor man struggling and screaming in silence as he tried and failed to warn his friend...  
  
After only a few minutes he heard the sound of a large body hitting the floor above him and for a moment he hoped that Cas had managed to put Dean down...but the sound of that same body being dragged along the floor, the then thump thump of it being pulled down the stairs had his heart sinking. It was only when Dean himself appeared in the doorway once more, with the unconscious Angel sprawled out behind him that Sam wailed with despair.  
  
He had failed to save them both...first his Brother and now...  
  
"Castiel. So glad you could join us. Now we can have some real fun!"  
  
  
\----------  
  
  
Castiel came to slowly, floating up from the darkness that had overcome him, and the last thing he could recall was a pair of cold black eyes piercing his Grace and a smell like Whiskey, old leather...and Sulphur.  
  
But now there was nothing, the eyes were gone, the smell only a ghost in his mind and what replaced it was a pain unlike anything the Angel had felt before. It was like a dull throb in his head, and a sharpness in his shoulders every time he moved but when he reached inside to draw on his Grace and heal his wounds...he found his way blocked. He had a moment of panic as he searched for the link, while the pain built in his head but no matter how hard he searched he couldn't feel the light inside him...it was gone.  
  
"Cas...Oh Cas! Angel?" Deans voice drawled above him, pulling him further to the surface but when he looked up he was convinced he had to dreaming. The thing above him, this black eyed abomination, was wearing his friend but it couldn't be real. He didn't believe it. "Oh believe it, Baby...Its all me. 100% Dean Freakin' Winchester! Just think of me as...Upgraded. New and improved." Cas tried to launch forward, growling and glaring at the Demon in front of him, but he was stopped in his tracks by a force pushing him down, and when he tried to snap he found his voice caught in his throat. "Ah ah! Now now, Angel, we'll be having none of that! You're going to behave yourself around me or I'll be forced to punish you." Dean said, smirking when the Angel glared at him defiantly.  
  
"And just what are you going to do, Demon Scum!" Castiel screamed in his head, knowing full well it could hear him. The Demon's eyes flickered for a moment before he chuckled lightly, the quite suddenly he backhanded the Angel across the face, knocking him sideways onto the floor. Castiel couldn't quite grasp what had happened at first, because he had expected to hurt but no where near as much as he did. This Demon, he decided, had to be unbelievably strong...but when he reached up to cup his swollen cheek, his fingers trailed over something metallic that was clasped around his neck. The Demon snorted as Cas put both hands up to his neck and found the reason he couldn't access his Grace. The Demon had collared him, he was completely trapped now and he didn't think it could get any worse than this...  
  
"Sammy! Don't be rude now, say hello to Cas...You two will be spending a lot of quality time together from now on so I suggest you start it off right." The Demon said, and with that Cas broke down. The Angel looked behind the Demon to wear his closest friend and ally was chained to the wall, struggling for release and crying as he stared at the broken and frightened Angel on the floor at Dean's feet. The pair stared at each other and knew in their hearts that there was no way out of this now, they had no hope now of a rescue. No one was coming to save them this time.  
  
They were trapped.  
  
Dean stepped back between the Hunter and the Angel and smiled down at the shivering lump on the floor, smirking when Castiel looked up at him with tear stained eyes, but there was no pity spared for the man as Dean smiled widely.  
  
"Lets get started..."  
  
  
\----------  
  
  
Dean's hand shot out suddenly and grabbed the poor Angel by the hair, yanking him to his feet and ignoring his pained cries as he dragged him across the room and threw him up against the opposite wall. Instantly he was pinned in place by the Demon's horrid power, a sickly tingle that crawled over his skin and made him shudder, but when he pulled out the Angel blade and hovered the point only inches from the Angel's throat Cas was suddenly very grateful that he couldn't move. Dean trailed the tip slowly down to the Angel's clothing and got to work slicing and ripping off his shirt, working till the material was in rags all over the floor and the man was completely exposed from the waist up. Then he moved onto his pants, loosening them off and slipping his hands inside to cup the Angel's genitals, chuckling when the Angel bit off a moan and his manhood twitched in the Demon's hand."  
  
"Time enough for that later, Baby...Right now lets get you naked okay? It'll be so much better when I can see what I am working with..." The Demon spoke softly, as though trying to comfort Castiel but his hands were rough on the Angel's skin as he pulled his pants down his long legs and finally off, leaving him pinned to the wall in only his white boxers. Dean smirked as he watched a trail of tears wet Cas' face, and he moved in to plant a small kiss on his cheek, licking obscenely over his skin and tasting the salt of them. "So sweet, Angel. You are going to be fun to play with, fun to break..." Dean grabbed the growing bulge in Cas' boxers and squeezed hard, laughing when the Angel squeezed his eyes shut and screamed to Heaven, unbelieving of the pain he was feeling. As quickly as it came it was over, and Dean was cutting the last of Cas' coverings from him, leaving him naked and shivering before him. Dean took in the sight of the naked Angel, admiring the miles of smooth pink skin that was now available to him and the beautiful curves he had been hiding under all those clothes. "Damn, Cas! You've been holding out on me, huh?" Dean whistled and spanked the side of Cas' ass, chuckling when the Angel cried out again. "Ain't he pretty, Sammy?" The Demon clicked his fingers and the boy behind him was talking again.  
  
"Dean, please! Stop this! Its Cas' for christ sake he's your friend you can't do this to him!" Sam pleaded with the Demon from behind him, completely missing the mischivous smirk that crossed his face, making Cas' blood run cold.  
  
"You're wrong, Sammy. I can do this to him, this and anything else I want! So if I want to turn him around right now and fuck his little virgin ass dry well...What exactly could you do to stop me..."  
  
"Please!" Sam begged, yelling out when Dean grabbed a hold of Cas again and dragged him forward towards Sam, stopping with the Angel only inches from Sam's face.  
  
"What's his ass worth to you, Sam?" Dean asked and Sam locked eyes with his crying friend before turning to look up at Dean.  
  
"Anything..." Sam choked out. "Anything you want...just please don't hurt him." Dean thought about it for a moment before shrugging his shoulders and letting go of the grip he had on Castiel's hair, allowing the Angel to fall to his knees before Sam.  
  
"Okay, Sammy. I can play nice for you boys, so here's the deal. I won't fuck him...if you do it instead."  
  
Sam was too shocked to say anything, and the whole room seemed to drop a few degrees. The only sounds were the dry sobs of Castiel, who was crouched on the floor and shaking his head as though he could make it all go away if he just believed it. The Hunter couldn't even react when Dean snapped his fingers and released him from his chains, dropping him to the floor in front of Cas.  
  
"Go on, Sammy...Your Bitch is waiting. Why don't you give the poor guy a kiss first, he's so nervous." Dean said in a mock sweet voice, watching as his Baby Brother reached out and gently wiped the tears from Cas' face, whispering to him comforting words about how it'd all be okay but soon enough Dean was becoming impatient and his voice cracked through the air like a whip. "Tick Tock, Sammy! Start working or I'll do it myself! And trust me he isn't gonna like it my way..." The Demon snapped his fingers once again, conjuring himself up a glass of Whiskey and walking some distance away to where a Throne had appeared. He took his seat, looking every bit the Demonic King, and waved his hand for them to get on with it.  
  
Sam turned back to Cas and reached for him, cupping his face and turning the Angel's red and scared face up so he could look him in the eye. His heart broke as he saw the fear in Cas' eyes and he very slowly inched closer to him, leaning in to kiss over his face and whisper to him.  
  
"I'm so sorry, Cas...I don't...I don't wanna hurt you. But I don't want him to hurt you either...I don't know what to do! Please, Cas...I...I'm sorry!" Sam started to cry as he took the quivering Angel in his arms and pushed him backwards, laying him out across the floor, pinned underneith him. Dean perked up as he watched Sam press his lips to Cas, and after a moment slip his tongue into the Angel's mouth. His Brother coaxed and calmed the scared man beneath him with gentle touches and kisses till he had him moaning softly into his mouth and reaching out to pull him closer. Dean's eyes slid down Cas' body to where his cock was lengthening and thickening against Sammy's leg. The younger Winchester slid his hand down between them and took ahold of it, swallowing up Cas' every moan and whimper as jerked the Angel till he was fully hard. Sam pulled back for a moment, leaving Cas laid out on the floor panting and flushed as he pulled off the last of his clothing, leaving himself as bare as Castiel. He tried to block out the approving sound from his Bro...that -thing- that was watching them, and concentrated completely on Castiel. Sam took a moment to admire Castiel in a way he'd never believed he could, and the Angel saw him looking if the blush on his cheeks was anything to go by. Cas reached out for Sam and took him by the arm, pulling him down to meet him again and moaning loudly when the Hunter slotted himself between his legs and rutted his hard cock down against his own. Sam took his time stroking and kissing every inch of Cas' skin that he could reach and Cas squirmed under him in his pleasure, each almost forgetting that they were being watched, but watched they were and Dean was growing restless again. Their playful touches and gentle kisses was starting to bore him once more and he winked in Sammy's direction, laughing when a 'crack' sounded in the air and Sam cried out in pain, a large red mark appearing on his backside.  
  
"Get on with it, Sam! You've got a job to do, remember? Put that Bitch on all fours...Now!" Dean barked and Sam looked down at Cas, suddenly embarressed and apologetic as he flipped the Angel onto his front and took a hold of his hips, lifting him easily so he was bent over before him. "Now Cas, I want you to be a good boy and suck on Sammy's fingers, get em' nice and wet cause its the only lube you're getting." Dean ordered as Sam crawled up closer behind Cas and leant over him, reaching forward to put his fingers before Cas' mouth. The Angel whimpered fearfully but took the Hunters fingers into his mouth, and Sam couldn't help but to gasp a little when he felt the suction around those digits. A dark and evil part of his mind wondered just how good that mouth would feel around his cock and Dean, the Demon that was his Brother, answered him. "All in good time, Sammy. Thats enough! You got five minutes to work him open Sam, no more no less. So you better do a good job." Sam glared up at the Demon on the throne but it was cut short when an invisible hand stuck him clean across his jaw, knocking him senseless for a minute, but when the Hunter spat blood on the floor and lifted his eyes to the Demon again it was Cas' turn to feel the Demon's wrath. The Angel screamed suddenly and Sam whipped around just in time to watch long slash marks appearing down Cas' back, as though someone was whipping the skin from him.  
  
"Stop it!" Sam screamed, grabbing a hold of Cas and trying to pull him back but the Demon was holding him in place and showing no mercy. "Please! I'm sorry!" And with that the Angel collapsed into a crying heap, leaving Sam free to gather him up into his arms and hush him gently.  
  
"Learn your place, Sam, and quickly or every time you step out of line it'll be Bitch there taking the heat. Understand?" Dean barked and Sam nodded, silent and with his eyes on the floor. "Good Boy. Now, continue." Sam's heart broke as he pushed Cas away, the Angel struggling to stay in his arms but he had to finish this otherwise the consequences would be far worse. He pushed Cas back into position, and offered his fingers to the Angel again - sickly thankful that Dean allowed them another chance otherwise poor Cas really would be taking it dry. Once his fingers were coated with spit, Sam took a moment to stroke down Cas' back, trying hard to calm his nerves, but the second he slid his fingers between the Angel's cheeks and circled his hole the man was shaking and crying all over again. Sam chanced a look up at Dean one last time, a silent beg for this to end, but when he found the Demon lounging back on his throne with his hard cock in his hand he gave up trying. He started by slowly slipping in one finger, hushing Cas gently when the Angel tensed up and whimpered, turning to him with pleading eyes.  
  
"Shh, Cas, Baby you gotta relax a little otherwise its gonna really hurt...please Angel, try and relax. I swear I will be gentle with you, I'll make it so very good for you Baby." Sam spoke softly to Cas as he slid his free hand under the Angel and found his flagging cock, taking it in hand and stroking him till he was hard again. He started to slowly thrust his finger in and out of the Angel's tight and twitching hole but the more he stroked him the looser he got, and finally he was able to push in a second digit alongside the first. He gave the Angel only a few seconds to adjust before he started scissoring him open, mindful of the time limit as Dean cleared his throat loudly. Sam shuffled up closer behind Cas and allowed his own hard cock to bump against Cas ass, and when the Angel moaned and pushed back on his fingers he quickly slid in a third digit. Sam leant down and started kissing over the back of Cas' neck, nipping at the skin and moaning softly when he twisted his hips and slid his cock all over Cas' skin, pumping the Angel's cock as he finger fucked his ass. When Sam twisted his fingers inside the Angel's hole and nudged against the little bundle of nerves, Cas bucked wildly back against his hand and moaned loudly, thrusting his own hips back onto Sam's hand and forward to fuck into his fist.  
  
"I think the Bitch is ready for you now, Sammy. Don't want him too loose now do we, gotta keep him tight enough to fit snug around your cock. Line up, Sam..." Dean ordered and Sam slowly pulled his fingers out, fascinated by the way Cas' hole - so tight and nervous at first - now sucked at his fingers as though trying to keep them inside. Sam sat up and placed his hands on Cas' hips, reaching down to guide the head of his cock to Cas' hole but hestitating, waiting for Dean's word. The demon chuckled and drained his whiskey, gripping his own cock tighter in his hand. "Mount him, Sammy!"  
  
Sam grimaced at the order but his hips pushed forward regardless, the pull of Cas' hole was far too tempting on his aching cock and as he slowly buried himself up to the hilt in Cas' ass - taking his time as the going was dry and a little painful even to him - he couldn't hold back the moans that escaped his mouth even as Cas cried out under him. Sam felt bad for the Angel, but he felt too good wrapped around him and even his pained cries were beginning to sound hot. The Hunter wasted no time in pulling out and slamming back inside, going a little harder and faster every time until he was pounding into the weeping Bitch below him. Sam shook his head to clear it, horrified at his own thoughts, and somehow he knew that Dean was playing with his head but he couldn't muster enough strength to push him out, not with the way Cas felt hanging off his cock.  
  
"Admit it, Sammy, you like it. You like having him trapped under you, you want to make him scream...I can give that to you, Baby Brother, I can give you everything you want. You can have him whenever you want, you can fill him up as often as you please...just join me. Say Yes, Sammy. Come home with your Big Brother and you won't have to suffer along with him." Dean said, his voice so close it was as if he were directly behind Sam, watching him wreck the Angel's ass with his near violent thrusts but even through the haze of lust and cries he found the pull he needed, and it came in the form of a tiny voice calling to him.  
  
"Sam..." Cas' hoarse and broken voice drifted up to him, the only sound the Angel could manage before the Demon's power washed over him again but it was enough to bring Sam back to his senses.  
  
"No!" Sam screamed, tearing himself backwards and yanking himself free from Cas, leaving the broken and bleeding Angel slumped over on the floor. When the Hunter looked up at the Demon he found Dean disappointed rather than angry.  
  
"Well, if thats how you want it Sam...fine. But don't say I didn't try to protect you." Dean snapped his fingers and Sam choked as he felt a sudden pressure around his neck. He reached up and found a collar just like Cas' locked around his neck, but he had no time to panic before Dean was dragging them both forward on their hands and knees, till they were knelt before him on the Throne. He sat up and spread his legs out, making room for them both before him as he worked his cock hard and fast. Sam saw the large member grow a little more as his Brother neared completion and then he felt his head being pushed forward, closer until his and Cas lips were just shy of Dean's skin. "Kiss it, Bitches...This is your only purpose now." Dean said as both his Brother and his Angel leant in and started to kiss and lick over his heated flesh, the sight of them naked, broken and collared before him enough to send him over the edge. As he climaxed, he made sure to give their faces a coat of cum each, he had to be fair after all. As Dean leaned back in his seat he summoned himself another glass of Whiskey and tucked himself away, smiling down at his cum covered Boys.  
  
"Well, what are you waiting for...Lick each other clean." Dean snapped, pride welling in his chest as he watched the pair turn to one another and start to lap at the cum on their partners face. He didn't miss the fact that Cas' cock was already starting to thicken again, and he thought with a laugh how surprising it was to find out just how much of a whore his Little Angel really was...As for Sammy, well...the boy would learn soon enough. "I want you both ready to go again in thirty minutes...I think its Sammy's turn to play Bitch, don't you Cas? Lets see if we can make him a whore like you..."  
  
Oh yeah, Dean thought, life was sweet.


	2. Crimes And Punishments

**Summary for the Chapter:**

> Dean sets his new pets up for the night and Castiel gets a taste of things to come...

**Notes for the Chapter:**

> So...After a ton of popularity, I have decided to add a little more story and a lot more porn to this ''One-Shot"...I HOPE YOU ARE HAPPY WITH YOURSELVES!
> 
> ALL WARNINGS APPLY IF YOU SQUICK AT VIOLENCE, RAPE, BLOOD OR ANYTHING AT ALL EVEN BORDERING ON ICKY DO NOT READ THIS FIC! I WON'T BE RESPONSIBLE
> 
> MAJOR PLOT TWIST INCOMING! DROP ME A COMMENT LET ME KNOW WHAT YOU THINK!

Before he left his new pets alone for the night, he snapped his fingers and rearranged the room so it more closely resembled a small cell. There was two mattresses pushed against the walls, a small cordoned off area with a toilet - Sam thankful enough for the privacy - and in the corner there was a pair of what looked like dog bowls. Sam's mouth went dry as he stared around the room, far too shocked for words. The only sounds were the dry sobs free Cas, whom Dean was cradling in his arms and speaking to gently.  
  
"Hush now, Angel, don't cry...this is only temporary. Once you are both trained properly you can have a real room of your own right next to mine, I promise. Would you like that?" Dean asked but when Castiel whimpered and shook his head, frantically trying to pull away from the Demon, Deans face contorted into a rage and he lashed out suddenly, slamming the Angel down onto the hard floor with a sickening crunch. Castiel wailed in pain but Dean gave him no sympathy as he started to yank the belt from his jeans before wrapping part of it around his hand, gripping it tightly with the buckle end hanging loose. Sam knew instantly what it was Dean planned to do with that belt and he tore across the room and throwing himself between the Demon and his friend.  
  
"Dean no please don't hit him!" Sam screamed, shielding the smaller man with his body and holding his hands up, body braced for a blow that didn't come. When he dared to lock eyes with the Demon he found himself shaking even more. Dean was not angry anymore...he was smiling, and that cold grin was enough to give Sam chills all up and down his spine. After a long pause Dean reached down and stroked his fingers through Sam's hair, ignoring the man when he flinched at his touch.  
  
"Such a good boy, Sam, trying to protect him. You're right of course I should not be punishing him...I should be punishing you." Dean said, and Sam cried out when the fingers in his hair suddenly tightened, balling into a fist which gripped him tightly. "Since you are so interested in protecting him, you're now responsible for him. Same as if you fuck up I punish him, well now when he fucks up I'll punish you." Dean dragged Sam to his feet and gave him a hard shove towards the back of the room. "Get over there, turn around and put your hands on the wall." Dean ordered and when it looked like Sam was going to protest the Demon turned on the Angel once more, belt raised over his head...  
  
Sam reacted on instinct, hand flying out to grab Deans wrist, pulling him up short so he couldn't land his blow but the moment Dean turned his furious gaze on the young Winchester, Sam let go and started to back away quickly. The Demon followed him stalking him like pray as he backed him up against the wall, teeth bared in a snarl. When there was no more room to escape Sam closed his eyes and turned his face away, unconsciously baring his neck to the Demon. Dean took the submission and growled a little approval before putting his lips to Sam's ear and speaking to him in a deadly voice.  
  
"Don't you ever -EVER-" Dean smirked when his sudden raised voice made Sam yelp and whimper, his knees shaking with fear. "...put your hands on me again. Do you understand me?" Dean snarled softly, and when Sam nodded swiftly the Demon backhanded him, knocking him to the floor. "You answer me properly, Sam! Do you understand me?!"  
  
"Yes!" Sam screamed, cowering at the Demons feet.  
  
"Yes...Master!" Dean corrected his pet, and it was a beautiful sight to watch his once proud Brother - now blushing and naked on his knees before him - turn his eyes down to the floor and mutter in a broken voice...  
  
"Yes, Master."  
  
Dean smiled down at the broken man and reached down to pet his hair, hushing him softly.  
  
"Good Boy, Sammy. You're learning fast, you always were such a smart boy." Dean praised his Pet, stroking down his face gently and cupping his jaw, tilting his head up so he could look into his eyes. "Now get up, turn around and put your hands on or watch me whip the skin off your little bitch there and leave him bleeding on the floor...Your choice." The Demon said, backing up a little and allowing Sam a moment to contemplate his choice. The younger man looked over to where Castiel lay curled up on the floor, naked and shaking. His eyes wandered over the Angels flesh, along the multitude of cuts scrapes and bruises - in particular the large hand prints on his hips...Sam's handprints...- and he bit his lip, fighting back a fresh wave of tears. He would do this for Cas because he had to protect him. He owed him that much. Sam slowly pulled himself to his feet and - with one last pleading look at his Brother - turned to face the wall. With his back turned he missed Deans triumphant expression as he surveyed the smooth skin, hard shoulders and the graceful curve of Sam's back and ass. Dean couldn't wait to bury himself inside his little Brother and watch the kid writhe and buck on his cock, but for now...  
  
"Sam. I am going to give you ten strikes in payment for Castiels infraction..." Dean said, being sure to send the cowering Angel a harsh look before turning back to Sam. "And twenty for putting your hands on me without my permission. I want you to count them out with me, and w when I am finished with you, you will get on your knees, kiss my cock and beg for forgiveness." Dean tapped the belt against Sam's back gently for a moment before pulling back swiftly and bringing the leather and metal smashing back down against his skin. A scream tore from the young mans mouth and in the background Castiel cried out and tried to close his eyes and cover his ears, wanting to hide from the sight and sound of his friend being tortured, but he found that no matter how hard he tried he could not force his eyes closed nor lift his hands to his head...he was paralyzed and helpless, forced to watch by the Demon who turned to wink at him before returning his attention to Sam. "...are we forgetting something Sam..." Dean asked in a sweet voice and Sam suddenly remembered that he was supposed to be counting.  
  
"O...on....one!" Sam managed to force out, and it was only a second more before Dean struck him again. "TWO!" The man screamed, but as the blows continued to reign down on his flesh and his back became a bloody and bruised mess, his voice got weaker and weaker until the last blow fell and his words were nothing but a dry croak from his wrecked throat.  
  
When Dean finished with him he pulled back the power he had been using to keep Sam on his feet and with that the kid collapsed to the floor, too weak and tired to even reach out to break his fall. Dean gave him a minute but grew restless quickly and walked over to the limp body, prodding it sharply with the toe of his boot as he started to loosen his jeans and pull out his cock. The way Sam had screamed and the thrill of the punishment had left the Demon rock hard and dripping, and he was determined that he was getting his cock in Sams mouth whether the boy was conscious or not. He'd skull fuck Sam's bloody throat till he came and gave the man a belly full while he cried but just as he was reaching down to yank his dazed Brother to his knees, Castiel appeared suddenly between them, frightened eyes locked with Deans.  
  
"No please! He's done enough please, no more...don't hurt him anymore..." Cas begged the Demon but Dean pointed to the aching cock in his hand and raised an eyebrow.  
  
"He still has some business to take care of Castiel...no move aside!" Dean barked but Cas shook his head, bravely shuffling closer to the Demon.  
  
"Then let me do it for you!" Cas offered, frightened eyes flicking between Deans face and his cock. "Please...Sam is hurt, he can't do this right not like I can, I can make this good for you...please. Please don't punish him anymore." The Angel made an interesting point, and Dean pretended to think it over while Cas sobbed on the floor at his feet. Finally the Demon stepped forward and put his cock in Cas face, the tip resting on the Angels perfect little lips.  
  
"The moment I feel teeth...I'll introduce Sam's ass to my knife. I'll fuck him so hard it he won't sit down for years...understand?" Dean threatened and Cas whimpered nervously, fresh tears staining his cheeks.  
  
"Yes, Master..." Castiel said and Deans eyes flashed black as the Angel parted his lips and allowed the Demon to feed him his cock. Dean didn't stop, not even when Cas gagged and tried to pull back forcing him to lock the Angels body in place, until his cock was buried deep in Cas throat and the muscles contracting and spasming around him made him want to shoot his load right then. Dean took a few minutes to enjoy the feeling before he pulled out and slammed back in, grunting and huffing as fucked Cas face without care for the choking man beneath him. Cas gagged and heaved, every thrust abusing his throat and making his eyes water. With his jaw locked open there was no defense against the Demons assault and all he could do was cry as he stared up at the monster who was raping his mouth. The sight of Castiel on his knees with Deans cock pistoning in and out of his mouth and tears in his baby blue eyes was enough to send Dean howling over the edge. He snarled like a vicious animal and buried his cock as deep as he could in the Angels throat, before emptying load after heavy load of hot cum down his throat and into his belly, forcing him to swallow it all or choke.  
  
When he was finally finished he pushed Castiel off him and the hysterical Angel collapsed back onto the floor, breathing heavily and heaving as his guts rolled, threatening to empty themselves onto the floor.  
  
"You better not sick that up, Castiel or I'll have to give it to you again!" Dean threatened, but after several minutes Castiel managed to keep it down and Dean gave him a pat on the head. "Good Bitch."  
  
The Demon took a moment fixing his clothes and tucking himself back inside his Jeans before he turned to look over his pets. Sam was still passed out on the floor, his back a bloodied mess from the belting he had taken, and Castiel was crawling slowly towards him, sobbing and muttering frantic apologies even though the unconscious man could not hear him. When he reached Sam he pulled the man up and laid Sam's head across his lap, stroking his hair gently until Sam started to come around again. The younger man's eyes flickered open and when he saw Cas' swollen lips, bloodshot eyes and the fingerprint bruising forming on his throat and cheeks from where Dean had gripped him tightly to yank him back onto his cock, the realisation hit him and he reached up to gently palm at Castiel's face.  
  
"Cas..." Sam choked out, his throat a mess from his screaming.  
  
"Sam..." Castiel started to speak but Dean cut them off with a cough, admiring the way they both jumped and cowered together away from him. He liked that they were afraid.  
  
"I think I should take a moment to explain to you both how it is we are going to do things around here. You two are not free anymore, you belong to me. You are my Pets and I will keep you as such for as long as I wish you to be here. Now, that does not mean that your life will always be harsh punishment and brutal fucking, no, I want to train you so eventually you will be my perfect little Toys and we can all have a wonderful life together. I know we have some way to go before that happens but I can be patient with you, trust me. We will start your proper training tomorrow so I suggest you both get some sleep tonight, you are going to need your strength." Dean snapped his fingers and a metallic rattle had them turning towards the noise. The bowls in the corner where now full with some kind of stew like substance that was steaming just a little, a the room was filled with the delicious smell of gravy and cooked meat. Dean smiled at them benevolently and headed to the door, opening it and walking out with only one last word to the shocked men left in the room behind him.  
  
"Goodnight, Pets."  
  
  
\----------  
  
  
The Demon made its way upstairs and into the bedroom it had claimed as its own, locking the door behind itself and bracing it shut with a click of its stolen fingers. It pulled off the human garments it was wearing which were now stained with the blood and gore from the Angel and the Human he had locked in the Dungeon. As it made its way to the dresser, the old cracked mirror that had pride of place in the centre of the decorative wood reflected back at him...but it was the face of the monster which it saw in the glass, and the figure which writhed and clawed under his skin was now glaring at him out of his stolen eyes.  
  
"You fight all you want in there, filthy parasite...I do love it when they struggle. It tingles." It said, watching as the Human soul trapped inside him erupted with hate and a murderous longing that made him laugh aloud. "Ohhhh...Am I gonna have a ton of fun with you."


	3. The First Night

**Summary for the Chapter:**

> Sam and Cas spend the first night alone, while the Demon messes with Sam's head. But after an ill-advised escape attempt, Sam is about to learn that it isn't just his mind that the Demon is interested in fucking with...

**Notes for the Chapter:**

> Wow this is actually more popular than I expected! Thank you very much guys!
> 
> Warnings for this chapter is low, but the next one is intense so buckle up. This is more of a bridging chapter and a small look inside the emotional state of Sam. I hope you enjoy x

Castiel cried through the night curled up on his own mattress with his arms wrapped around himself for comfort and warmth. The cell was cold and dark and Castiel was too frightened to sleep but although his cries kept Sam awake the young hunter didn't crawl over to comfort him...he couldn't bring himself to be near him. It made him sick to his stomach to think that his friend was in need but he wouldn't go help him, but there were too many conflicting emotions raging inside of him and he didn't honesty know how he would react if he were to lay even a finger on the Angel right now. He felt like he would either burst out in tears because he helped put Castiel in this mess...or he'd lash out violently and hurt him more. After all it was Cas' fault that the Demon was angry with them, and if he had just nodded along maybe Sam's back wouldn't hurt so much...  
  
"Sam..." Castiel's voice drifted over to him across the silent room, timid and rough from tears. "...are you awake..." The heartbreak in that voice did it for Sam, and the man was crawling quickly towards the sound of his friend. As he draw closer, he felt Castiels fingers ghosting over his face and without thinking he chased after those fingers with his lips, drawing a surprised laugh from the Angel as he kissed each fingertip he caught. Castiel brought both hands up to cup his face and suddenly there was the feeling of soft breath against his face and the softest little lips pressed against his own. They didn't try to deepen it, the kiss was not so sexual but rather it was playful and comfortable, and Sam moved forward again on his knees with his arms gently gripping the Angels arms and pushing him back till Cas was flat out on his back and Sam could lay down beside him. The mattress was small and the pair had to huddle close together but neither cared, it was much warmer with two and as they relaxed a little Cas shuffled upon Sam's side and put an arm around him, resting his head on Sam's chest. The young Winchester stroked his fingers through the Angels hair and placed a gentle kiss on the top of his head.  
  
"We're going to get out of here, Cas. I swear...I am going to get us out of here. I'm gonna save us..." Sam whispered in the dark and Castiel's grip got a little tighter, an acknowledgment that he understood. Sam knew his throat still hurt from earlier so he was surprised to hear him speak.  
  
"And Dean...We have to save Dean..." Castiel croaked, his voice harsh as he spoke. Sam tensed a little bit as he thought of that thing upstairs and for a moment he felt like hitting the Angel, knocking some sense into him - The Dean they knew was gone and what was left was the reason that they were huddled together for warmth in a freezing dungeon on a stinking mattress. The sooner Castiel realised that the easier this would be on them. "It isn't him Sam..." Castiel insisted, his heartfelt sincerity only serving to annoy Sam further. "That thing, whatever it is, it is not your Brother! I can feel Dean still, trapped somewhere like we are now...we have to save him to Sam. He is hurting so bad..."  
  
"Yeah, and what about me huh?!" Sam raged inwardly but he didn't voice his thoughts, instead he choked them down and tried to reason with himself. Castiel was obviously completely traumatized, an effect of the rape and his sudden humanity. To suddenly find yourself Human, only to be imprisoned and violated by your best friend and closest family well...it was enough to break anyone's mind. Sam took a moment to compose himself then he smiled - though what for he couldn't say, the Angel could not see him in the dark.  
  
"Of course we'll save him, Castiel...we always do. We'll fix this and it'll be just like old times...Why don't you get some sleep, Angel. You'll feel better in the morning." Sam suggested and he barely made out the hushed voice that was muffled against his chest.  
  
"I wish morning wouldn't come...I'm scared Sam." Castiel admitted and Sam felt more like himself again, the out of sorts anger from moments before fading faster than a bad dream.  
  
"Don't worry, Cas. Whatever happens, I'll protect you. I'll always protect you." Sam vowed, and slowly the pair drifted into an uneasy sleep, unaware of the dark eyes watching over them and listening to every word they said...  
  
"We'll see about that..." It said, smirking when its presence caused the Angel to whimper in his sleep. "We will just see..." And with that it vanished, leaving it's pets to sleep. They were going to need it.  
  
  
\----------  
  
  
When the lights came on in what they could only assume was the morning, the pair cringed at the sudden blinding light that roused them from their slumber. Castiel groaned and burrowed down into Sam's side, shielding himself from the harsh reality but he wasn't there long, because with the light came a beautiful smell and the Angel peered over the mans chest to see their two bowls sitting on the floor, filled with porridge. The Angel moved to crawl over Sam but the hunter pulled him back, the grip on his arm just shy of painful.  
  
"What the Hell, Cas? You are not seriously gonna eat that?" Sam barked and Castiel shied away from the vemon in his voice.  
  
"...I'm hungry Sam..." Cas said, a pitiful explanation that made Sam scorn.  
  
"So what, you are just gonna crawl over there and eat out of a bowl like a good little doggie! No! I won't! And neither will you!" Sam said, yanking Cas back down onto the mattress before getting up and storming over to the food. Cas watched in horror as Sam picked up both bowls of food and walked over to the small toilet, emptying the contents and flushing it away in an instant. The Angel choked on a small sob which Sam ignored as he started pacing around the room, searching along the walls and scanning the ceiling, clearly searching for something.  
  
"What are you looking for?" Cas asked from his bed and Sam continued to search around for anything which might help.  
  
"I don't know, just anything that might help us get the Hell out of here...There has to be something." Sam said, more to himself than to Cas who was watching him with worried eyes.  
  
"Sam..." The Angel started tentatively. "How do you plan to get us out of here...when you are weakened? You have to eat eventually..." Sam growled and rounded on the man, watching as Cas lowered his head and backed up slowly.  
  
"What is with you?! Huh?! You think I can't do it, you think I am..." Sam raged, the Angel's timidness driving him crazy. "Look, you wanna stay here and cower like a dog under Dean's boot you go ahead and be my guest but I am getting out of here! You are either with me or against me!" Sam finished and went back to his search, leaving Cas watching him fearfully from the corner. When Sam was about to give up he walked by the toilet stall and stopped in his tracks. Just inside the door there was a sturdy metal holder, and it was not bolted down which meant Sam could easily move it around. When he reached in and picked it up he found it was decently weighted, and it would be absolutely perfect...if he could time it just right...Sam tensed as he heard the sounds of the heavy door being unbolted, and he turned to Castiel with a hard gaze. "Distract him!" And with that Sam moved swiftly across the room, flattening himself out against the wall behind the door just in time for Dean entering the room. The Demon locked eyes with Castiel and suddenly the Angel was moving forward on his knees, throwing himself at Dean's feet and shaking with fear.  
  
"Dean I am sorry! I didn't want this to happen!" Cas begged and the Demon had no time to wonder what it was the Angel was crying about before something hard smashed into the back of his head, stunning him for a moment. In the heat of the moment, seeing the Angel like that, he hadn't turned to seal the door behind him and when he turned around to work out what the Hell had hit him he saw the back of Sam disappearing out of the doorway...leaving him and the Angel alone in the room. Dean was in no hurry to chase after the running man, after all there was no where on Earth he could hide and even if he made it out of the bunker - which he would not - Dean would track him down and drag him back. Instead of taking off after him he turned back to the cowering Angel on the floor and thought for a moment on what he would do. A quick search of his mind showed the Demon enough to know that the Angel truly hadn't wanted to cross him again, but he was conflicted...frightened...so instead of giving him more fear he reached down and placed a gentle hand on his hair, petting him softly.  
  
"Shhhh its okay Cas, I am not mad at you. Poor Baby, shhh don't cry. I am sure Sam doesn't -really- hate you..." Dean explained and when the Angel squeaked and looked up at him with hurt and confusion in his eyes Dean went on. "I am sure he was just desperate to get away and he didn't mean to leave you behind. No doubt he thought you were right behind him...I am sure when he realises you're missing he'll be back...Right?" The Demon watched with concealed glee as Castiel broke a little more, sobbing at his feet and shaking from head to toe until Dean took a little pity on him and lifted him up into his arms, cradling him close. "You know you don't have to be scared of me Castiel, so long as you are a good boy for me I'll always take care of you. I have only ever hurt you when I have had to...so you learn to be good, but I don't like to do it. Remember I said the faster you learn to behave the sooner r you can leave this nasty room and come home with me...I meant it. Now I am gonna go catch up with Sammy and bring him back here...and I am going to leave the door open. I am trusting you to stay put!" Dean caught the Angel's jaw and tilted his head up so he was staring into his eyes. "There is no where to run, Castiel. And if you ever want to eat and sleep comfortably again I suggest you play nice...understand?" Dean's eyes flashed black for a moment before slipping back into their beautiful green when the Angel nodded his assent, and the Demon placed a soft kiss on his lips. "Good Boy..."


	4. Learn Your Place

**Summary for the Chapter:**

> Sam is about to learn his place in the Demon's world, and Castiel comes to his rescue in the most unusal way. But will it backfire on him after Sam drops like a stone...

**Notes for the Chapter:**

> WARNINGS! WARNINGS! ALL THE WARNINGS! THIS CONTAINS INCEST, RAPE, PRIOR UNDERAGE INCESTUOUS SEX/SEXUAL CONTACT! DO NOT READ IF EASILY UPSET, I AM BEGGING YOU!

Dean found Sam upstairs trying to force his way through the door to the main room, but the fact that he found in it the first place was surprising even to the Demon. When he had first taken the Hunter and the Angel as his prisoners he rearranged the layout of the Bunker they called Home so that even if one or both of them managed to escape the room they would be confused and it would be harder for them to make it to the front door. He should have taken into account that this had been the man's home and even if they doors were changed about he still knew the place, and once Sam was safely back in his cell the Demon would change the building again, or maybe he would move them to a completely different location all together...somewhere in the depths of Hell, somewhere where they would be too scared to escape...Yeah, now there was an idea...but first things first.  
  
"Now, Sammy! I am surprised at you!" Dean barked, startling the young man who took off running once again, heading down the Hall and away from the Demon who stood watching him with a humorous look on his face. He waited for Sam to disappear from sight again before he started to walk after him, calling out to him as he went. "Sam! This is pointless! You have no where to go and you are only making it worse for yourself! You come here right now and maybe I will go easy on you!" Dean said and somewhere in the distance a voice called back, sealing its fate.  
  
"Fuck you!" Sam yelled and Dean chuckled, eyes flashing to black again. It focused all its energy on the smell of fear in the air, and followed it with lightening speed until he appeared like smoke behind Sam and grabbed him by the arm, pulling him up short.  
  
"Very poor choice of words, Sam!" The Demon growled before disappearing on the spot with Sam in his grip, pulling the man back towards the cell where he was pleased to see Castiel was still where he put him. "Good Boy, Cas! Very good, behaving so well for me." Dean praised the Angel as he dragged Sam over to the mattress in the corner and threw him down, turning his hard gaze to the Hunter. "You know I really am very sorry about all this Sam, I really didn't wanna have to do this." Dean explained as he started to pull at his belt and undo it, and Sam felt like snapping at him to do his worst...until Dean's fingers started to work on his zip. The Hunter reacted and tried to charge forward, screaming when the Demon caught him with one hand and spun him around, throwing him back down onto the bed as though he were nothing. "Its my fault, really, you don't know your place! I taught Castiel his when you first became mine and now he is learning fast aren't you Baby?" Dean smiled over at Castiel who was cowering in the corner with his eyes closed.  
  
"Please...Dean don't do this! Not to Sam..." The Angel whimpered but Dean ignored him in favour of watching Sam's eyes widen when Dean pulled out his already hard cock and gave it a few tugs.  
  
"Get over here, Sam." The Demon ordered but Sam shook his head, backing up against the wall and clamping his mouth shut when Dean darted forward and put the head of his cock against Sam's lips. "Don't make this any worse on yourself Sam! Either suck it or take it dry, I don't give a fuck which!" The Demon growled and Sam whimpered, shaking his head again and turning his head away, closing his eyes against it. Dean's eyes flashed and he lashed out, balling his fist up and punching Sam in the face hard, smirking when the young man screamed and the blood poured down his face. Dean gripped Sam's face and yanked him around, forcing his mouth open and guiding his cock inside until he was buried in Sam's throat and the Hunter was struggling against him, fists pounding against his body uselessly. The Demon was like steel under his onslaught. A hard grip on the back of Sam's neck had the Hunter held still and the Demon started to thrust painfully hard into his mouth, giving him no time to breathe or think as he used him ruthlessly. "You'll thank me for this later Sam, after I stick my cock up your ass you'll be so damn grateful I let you wet it first." Dean growled, moaning when Sam whimpered around his cock and the vibrations rippled along his flesh, making it harder not to cum in his mouth. When he was finally soaked enough he pulled out and glared down at the coughing and crying man at his feet. "I want you on your hands and knees Sam, you are about to learn what happens to bad boys around here..." Dean snapped but before Sam could even plead Castiel was crawling around Dean's legs and pawing at the Demon.  
  
"Master!" The Angel cried, startling both men into silence. "Please...let me prep him for you?" Cas asked and Dean stared down at him with a hard and calculating gaze. "It won't feel good this way, not even for you...let me help, please." Cas said, kneeling up so Dean's cock was hovering only inches from his mouth and he leant in to flick his tongue over the tip. Sam glared at his back as he watched him, up and begging like a dog to help Dean rape him, but when Cas looked around at him Sam saw the truth in his eyes...in his own way Cas was trying to help him. This was going to happen with or without prep, at least this way it might not hurt as much. Dean reached his decision and slid his fingers through Cas' hair, moaning softly when the Angel lapped at his cock head again.  
  
"You have five minutes to get him wet for me, Baby...You do a good job and I might even let you suck him off while I fuck him, would you like that? My little cock whore..." Dean said, smiling when the Angel nodded and kissed his cock softly.  
  
"Yes Master, Thank You Master!" Cas said, backing away quickly and crawling over to Sam. The Hunter was tense all over and he backed away when Cas drew near him, betrayal written all over his face and Cas decided he had to take this as slow as he could afford. He thought for a moment and then it came to him...  
  
Cas sat back on his knees and reached out his hand, splaying his fingers and just waiting as Sam watched him, confused at first but as understanding descended on him Cas nodded, wiggling his fingertips lightly and smiling when Sam' lips twitched a little. Slowly, the Hunter crawled out of his corner and slowly made his way to Cas, catching the Angel's fingertips and pressing soft kisses to them, a mimic of their nighttime play. This time though Castiel pushed his fingers forward until they slipped into Sam's mouth, and he moaned softly when the Hunter started to suck on them, swirling his tongue along each digit slowly. Cas moved forward until he was almost sitting in Sam's lap and he slid a hand down between them until he found Sam's soft cock. He wrapped his hand around the man's flesh and gripped it tightly, jerking it while he kissed along Sam's neck and up under his ear.  
  
"Just pretend its only us here Sam, you and me alone in bed...I want you to imagine what you would do to me if you had the chance. Would you like to feel my mouth around your cock, Sam?" Castiel asked as he jerked Sam a little faster, smirking when the mans hips thrust forward and he moaned softly around Cas' fingers. "Well you can. Just as soon as I'm finished playing with you." Castiel pushed Sam back and the Hunter hit the mattress with a soft gasp, barely adjusting before Castiel was pushing his legs open and lifting them up. "Hold them." Cas ordered and Sam obeyed, eyes going wide when Cas disappeared down between his legs and ran his fingers over Sam's exposed ass. The Angel's breath puffed against Sam's skin and the Hunter's own air punched out of him as Cas' soft tongue pressed against his hole and wiggled in just an inch, drawing the loudest moan from Sam and the barest 'fuck' from Dean, who was watching from the sidelines and barely aware the the five minutes and come and gone...just as Castiel had hoped he would. The prep may have been for Sam's benefit, but the show was all for Dean. If he could have more time to work Sam open he could spare the Hunter the pain he had endured, and that would be more than worth this act. Besides, Castiel thought to himself as he lapped at Sam's hole and pushed his tongue past the rim, listening to the beautiful sounds of an out-of-his-mind-with-pleasure Sam Winchester...this really wasn't all that bad. Sam couldn't believe how good it felt to have Cas' tongue inside him and he cried out when the Angel slid a slick finger inside him alongside his tongue, working it in and out in time with his tugs on Sam's cock with his free hand. After a few minutes he added a second and scissored him open, working his spit inside and chasing it with his tongue till the Hunters ass was a sloppy mess and every thrust of his fingers into the twitching ass was wet and easy on the man. Sam was a writhing mess above him and when Cas finally added his third finger the Angel's face appeared again, smirking up at Sam. "You like that Sam? You like having my fingers in your ass?" Castiel asked and when Sam nodded, moans coming out in whimpery cries, Castiel drove his fingers into him hard, nailing his sweet spot head on and smirking when the man screamed. Castiel was so tempted to dive back between the Hunters legs and bury his tongue in that sweet ass but a hand on his shoulder brought him screaming to a halt. Dean was pulling him back and away, and both men whimpered as they were parted, Sammy tensing up again when he opened his eyes and found not Castiel above him but Dean...  
  
"You want Cas back on your cock, Sammy?" Dean asked and Sam's eyes darted to the side, finding Castiel sitting back and watching with tears in his eyes and a hard cock jutting up against his belly. The Angel was flushed and Sam was glad to see that it was not only him that was effected by this whole thing. When their eyes met Cas whImpered and thrust forward a little, clearly as desperate for Sam as Sam was for him, and finally Sam turned back to Dean, eyes on the floor.  
  
"Yes..." Sam muttered, eyes filled with tears.  
  
"Yes what?" Dean growled and he saw Sam's shoulders tense, poised for a fight, but a soft cry from Cas had him slumping in defeat.  
  
"Yes, Master..." Sam said and Dean smirked, reaching down and tipping the mans chin up so he was facing him.  
  
"Then turn round and get your ass in the air, I wanna see that pretty hole." Dean ordered, gloating silently when Sam obeyed straight away and turned away from him, lowering his front onto his arms and keeping his ass poised in the air, ready for Dean. The Demon knelt down behind the man and parted his cheeks, stroking his thumb over Sam's glistening hole and dipping in slightly, chuckling when Sam twitched under his touch and moaned very softly. "Good Boy, Sam. Thats what I like to see, so responsive." Dean shuffled up behind Sam and took his dick in hand, pressing the head against Sam's hole and frowning when the man flinched away, whimpering fearfully. But like a good little Pet Castiel dived in, crawling up in front of Sam and kissing him while whispering softly to him.  
  
"Its okay Sam, its not so bad. It hurts at first but it'll feel really good after awhile, I know it did when you did it to me. Having your cock in me Sam...you were so big and I was so full...But it was good Sam, it felt nice when you stretched me out." Castiel whispered to Sam, licking along his lips and pulling him into a kiss as Dean pushed forward, groaning when he buried himself up to the hilt in Sam's tight ass. Dean didn't stop until he was fully seated and Sam was wrapped around his cock, and the man was trying hard not to moan aloud as Castiel reached between his legs and found his cock already hard and dripping. The Demon chuckled and gave Sam's ass a little slap, thrusting forward once to hear the gasps from the man below him. A quick glare at Castiel had the Angel backing off and he leant over Sam's back to whispering in his ear as he started to plow forward into his Brother's ass.  
  
"Its okay to like it, you know?" Dean said, and when Sam shook his head violently, biting his lip to silence himself as Dean's cock moved inside him and brushed along his sweet spot. A sudden hand on his cock had him crying out and thrusting down into the grip, all his dignity flying out the window as he started to writhe between the hand working between his legs and the cock buried in his ass. "There you go, see Sammy you like it! You can be a good Boy when you just let go and accept it." Dean ran a hand over Sam's back, moaning as he watched Sam thrust back onto his cock again and again, fucking himself into a frenzy. "And lets be honest...its been a long time since you crept into bed and begged me to touch you..." Sams eyes went wide as Dean pulled his darkest secret out and dangled it in front of him, the hands on his hips gripping him tightly and forcing him back onto Dean's cock over and over. "You remember Sammy, when I woke up that night and you were practically humping against my leg...the way you squirmed and cried when I took you in my mouth and sucked you till you came. What about all those nights you spent with your face buried in my pillow while I licked your ass...I miss that Sammy, my little whore. Well you are gonna learn your place pretty fast now Sam, and its right here on your knees taking my cock! Just like Cas...Angel why don't you get your pretty little mouth over here and suck off Sammy, he's been such a good Boy tonight." Cas obeyed quickly, the Angel crawling forward and lowering himself under Sam, finding the mans cock hard and leaking as it bounced with every thrust from Dean into his ass. Cas licked his lips and took Sam in hand, giving the huge man a few rubs before taking the head into his mouth and sucking on ir hard, swirling his talented tongue around the head and gathering up all the salty moisture leaking from the slit. The Angel moaned when Sam thrust forward and forced his mouth wide, the poor man struggling to take it all as Sam rode his mouth while Dean fucked his ass, and Cas didn't pull away once while Dean pounded into Sam and used the hunter like a toy to fuck Cas' mouth. The Demon was drawing closer and closer to the edge, but when Cas pulled off Sams cock and trailed his tongue back along his skin until he found the edge of Sam's hole, soft little tongue catching Dean's cock with every thrust, that was when Dean came with a snarl, filling Sam up and pounding him through his orgasm. Cas sucked on the rim and lapped at every drop of Dean's cum as it leaked out around Dean's cock, and when Dean finally pulled out completely the Angel dove in behind him, eagerly cleaning up the mess that Dean had left behind him. The Demon gave him a few minutes with Sam before he chuckled and took a hold of his collar, pulling him back and away from Sam, much to the dismay of both Hunter and Angel.  
  
"Now now, Sammy...its bad manners to fuck a mans mouth and not give him anything back. Get over here and thank Cas for convincing me to take it easy on your ass. You'd be bleeding on the floor by now if it wasn't for him!" Dean growled, smirking when Sam pulled himself around and crawled up to Cas. The young Winchester had barely started sucking on him before Castiel was humping his face and crying out, cumming down his throat with a drawn out moan. When Sam pulled back, choking and spluttering, he was a little dismayed to be ignored in favour of Dean petting Cas' hair and telling him what a good Boy he had been...What about Sam...  
  
Dean finished praising Cas and put the Angel back on the floor with a final stroke of his hair, before snapping them up dinner and turning to leave. Sam choked on a surprised noise and glared at Dean when the Demon turned back to smile at him, his eyes flicking down to admire the cock still stiff and aching between Sam's legs.  
  
"You can consider that your punishment for trying to run away...And God help you if you put one finger on yourself tonight. Trust me I'll know, and even Cas won't be able to save your ass from what I will do to you. Good night, Pets." And with that Dean left, leaving a stunned Sam crashing hard as he realised he had just fucked himself on his Brothers cock and all but begged for an orgasm...  
  
What the Hell was wrong with him!


	5. The Third Victim

**Summary for the Chapter:**

> Sam loses his mind and lashes out at Castiel, which only serves to push the Angel further into the Demon's arms. Meanwhile, unbeknownst to the two suffering boys, a third victim is clawing at the walls of his prison and trying frantically to save them. The question is...
> 
> How exactly is the Demon punishing Dean?

**Notes for the Chapter:**

> My girl Angi wanted a change in tone and a little more from Dean's point of view, so I darkened it up and showed her just how bad Dean's suffering has become. Hell ain't got nothing on me...They are gonna throw me into The Empty for this one.

Castiel gave Sam a moment to compose himself before he started crawling towards the stunned Hunter, slowly and carefully incase the man decided to explode, but he managed to get close enough to place a gentle hand on his back. Sam looked up at him with lost eyes but the confusion quickly contorted into a rage which had Castiel regretting putting his hands on the man. The younger man growled and grabbed Castiel by the wrist, his grip harsh and painful as his fingers bit into to skin making Castiel cry out in pain and struggle to pull away from him. Sam felt a sick sort of pride as he yank the Angel down, pinning him to the floor, before he lay down across him and put them face to face.  
  
"Whats the matter, Castiel...I thought you liked it this way? I thought you liked being forced down and put in your place...or is it just Dean's cock you'll beg for!" Sam growled lowly at the Angel, anger boiling under his skin when the man under him whimpered and shook his head.  
  
"No Sam please...This isn't you! Let me go please stop this!" Castiel cried as he squirmed and bucked under the man, trying to pull himself free from Sam's grip but when he felt the slick wet tip of Sam's cock slide between his thighs he froze, too terrified to move. It wasn't until Sam started forcing his legs apart that Castiel came to life again, screaming and thrashing against him in a desperate attempt to throw him off. Sam finally snapped and brought his hand down across Cas' face, the slap open-palmed and hard enough to knock the Angel senseless.  
  
"Stay still you fuckin' bitch!" Sam yelled, the use of Dean's nickname for the Angel enough to set Castiel to crying once again, and enough to jerk Sam out of his violent rage. He lay still atop the weeping Angel for only a moment before he tore backwards away from him, shaking from head to toe with fright as he stared in horror at the rising mark he had left on Cas' wrists and face. The young Winchester stared down at his hands, and flinched when he found his fingertips covered in blood...Cas' blood, and he was so lost in his thoughts that he didn't hear the sound of the heavy door opening behind him.  
  
When the door opened and revealed a very pissed off looking Dean Winchester, Castiel couldn't help but feel relief and he quickly got to his knees and crawled towards his Master, his face stained with blood and tears. Dean crouched down and allowed Castiel to come to him, the Angel falling into his arms sobbing and shaking, and Dean had enough time to see the blood on his wrists, bruising on his face...and the precum staining his thighs...  
  
A quick glare towards Sam told the younger Winchester not to move, and that was the only attention he got as Dean lifted the trembling Angel into his arms and held him close, whispering sweetly to him to calm him down.  
  
"There now Baby, its okay now you're safe with me...I won't let that bad boy hurt you." Dean whispered as he brought Castiel over to his mattress and lay down with him, cuddling him close and stroking a hand over his back. "When you're ready why don't you tell me what happened..." The Demon asked and Castiel buried his face into Dean's chest, whimpering fearfully.  
  
"...He was trying to rape me...he hates me! Sammy hates me! I'm no good I'm bad!" Castiel started to wail, his heart breaking at the thoughts and memories swirling around his head as he clung desperately to the Demon's shirt. Dean allowed him to cry himself out, and it was almost twenty minutes of crying and babbling as Dean stroked his back and hushed him gently until finally Castiel calmed enough for Dean to speak.  
  
"Shh now Baby, its okay, Sammy doesn't hate you...he is jealous of you..." Dean explained and when a Castiel peered up at him, confused and sniffing with every soft sob Dean smiled at him and stroked a thumb over his cheek, wiping his tears away. "Don't you see, Angel? You are so beautiful, and perfect and you are such a good boy for me...but Sammy is having a harder time submitting. Now I know its easier for you, you have spent your whole life following a leader so its easy for you to bend but Sam...that boy has a thick head and he likes to fight. He sees you getting all my attention and how sweet I am with you and he is jealous, so he lashes out at you. But I wont let him do that to you again, understand?" Dean said, his eyes flicking over to a cowering Sam who was watching them with a strange look on his face, one that hinged somewhere between completely denial, fear...and jealousy. When Dean turned back to Cas and started to hush him again, kissing all over his face and praising him Sam turned away, huffing and crossing his arms over his chest.  
  
 _"I am -not- jealous!"_ Sam thought to himself but a small and hurting part of himself spat venom when from the corner of his eye he saw Dean run a hand down between himself and Castiel, palming over the Angel's thickening cock. Whatever he was whispering in Cas' ear must have been good because the Angel's breathing had sped up and when Dean wrapped his hand around the mans cock Cas moaned aloud and started to fuck down into the tight grip. It was only moments before Cas was spilling over Dean's fist and the Demon grinned as his pretty little pet gasped, calling for his Master. Sam turned away again as he heard Dean's voice, thick with praise, whisper to his Angel.  
  
"Good boy." And Sam's heart all but gave out when he heard Castiel whisper back.  
  
"Thank you, Master..."  
  
  
\----------  
  
  
Castiel fell asleep quickly after that, with Dean humming a lullaby under his breath and Sam lay quietly listening to them with a heavy heart and tears in his eyes. He hated to admit it but it was becoming harder and harder to resist the Demon, especially when he saw just how gentle and loving the thing could be...It was certainly keeping Castiel happy. Sam swiped a hand over his face to try and catch any traitor tears that might have leaked down his face but when he looked up again and found Dean standing over him and glaring he couldn't hold back any more. The younger man averted his gaze almost immediately and started to sob, wrapping his arms around himself in an attempt to shield himself from the man but when Dean reached down and took him by the arm, yanking him to his feet, Sam started to whimper.  
  
"Dean I'm sorry I didn't mean to I don't know why I..."  
  
"Quiet Sam..." Dean said, pulling the man over to the wall where he had been chained after the Demon first brought him down here.  
  
"I hurt him I didn't wanna hurt him I'm sorry please Castiel I'm sorry!" Sam yelled back at the slumbering Angel who stirred only a little before falling back asleep. Dean pushed him against the wall, pinning his arms above his head and chaining them in place. The Demon reached out and grabbed Sam by the jaw, silencing him and forcing him to meet his eyes, and just like that Sam found he couldn't speak anymore.  
  
"I must admit you have me at a loss, Sammy-boy...See I know what I'd like to do to you right now but it conflicts with my plans." Dean said as he pulled a knife from the back of his belt and waved it in front of Sam's face, but there was no playful smirk or teasing grin to be found on his face, only a dead straight anger that had the chained man too scared to speak. The Demon placed the tip of the blade against Sam's throat and very slowly trailed it down his body as he spoke. "You know what they do to bad dogs who can't control themselves around pretty bitches, Sammy?" Dean asked as he brought the blade down until it was pressed against Sam's cock, the boy tensing up and whimpering fearfully as Dean slid the blade around until it was pressed up under Sam's balls. "If I didn't have such wonderful plans for this cock Sam, I'd cut it off right now and use it fuck you until you screamed. You'd spend the rest of your time here with it shoved up your ass..." The presence of the knife and the fear tipped Sam over the edge and suddenly he felt a wetness trickling down his thighs, and Dean was growling in frustration...Sam had wet himself. The boy started to sob uncontrollably as his face went red, but he couldn't control himself and Dean just frowned at him before shaking his head and sheathing his knife again. "You are disgusting." Dean said and Sam hung his head, the insult tearing at his heart as he cried, and he hated to admit it but he wanted to be forgiven...he didn't want to hurt anymore. But of course his voice was gone and Dean was not interested in his hurt eyes. "I will think long and hard about what I am going to do with you, Sam, but for now I can't even look at you. Goodnight Sam." The Demon turned and walked out, without looking back at Sam who was now struggling against his chains and silently screaming for him to come back. He didn't want to be left this way.  
  
He wanted his Master back...  
  
  
\----------  
  
  
 _Try as he might Dean couldn't close his eyes against the world, the Demon working his limbs wouldn't let him, and no matter how he clawed at the thing it made no difference in the end...he still had to watch. But tonight the Demon had other ideas in mind, something a little more cruel._  
  
 _Hours after he had left Sam chained to the wall, the Demon crept back down to the cell and opened the door, silently slipping inside and staring around. Sam was hanging off the wall, barely conscious and a little nudge from the Demon's power was enough to put him under completely, leaving him asleep and unaware of his surroundings. Dean growled inside his own head and started to rage inside again, swearing every kind of vengeance against this evil thing but it only made the Demon laugh._  
  
"Fight all you like, Baby, feels so good to feel you squirm." The Demon laughed, before turning his attention on the slumbering figure in the corner. It made its way over to Castiel and stared down at him for a moment with a little smile on its lips. "He's a pretty little thing isn't he...I can see why you like him so much." It said as it knelt down at the Angel's side and slowly ran and hand down Cas' side, settling on his hip. The Angel shivered softly in his sleep and shifted, stretching out his body like a cat and sighing softly, and the Demon smirked as he guided the Angel onto his front and palmed at his ass, still red from the all the attention it had been getting recently.  
  
 _"You get your filthy hands off him!!" Dean screamed in his head as the Demon gripped Cas' hips and lifted the Angel onto his knees, face still buried in the mattress, and the Angel reacted on instinct by spreading his knees out a little and canting his ass into the air._  
  
"See how well he behaves, Dean, even in his sleep he is being a good a little whore..." The Demon chuckled, reaching out to circle one finger around the Angel's twitching hole before sinking in up to the knuckle and starting to fuck him open. Cas' mouth fell open and he started to whimper and moan in his sleep, hands clutching at nothing as the Demon added a second finger, then a third, all the time listening to the sweet cries of the Human in his head. "You can't tell me you don't want this Dean, I'm in your head remember? I've seen your dreams, your waking fantasies...I know about every single time you watched him and dreamt of mounting his ass, fucking him like an animal till he begged for your cum. Well don't worry Baby, tonight you get your wish. You want him, you can have him..."  
  
 _"What the Hell does that mean?!" Dean growled viciously and he felt the Demon smirk, then suddenly the world started to clear again. Dean felt himself again, almost like he were in control of his body but he wasn't able to stop his fingers from twisting inside Castiel and finding that sweet little spot that made the Angel buck back against his hand. "What are you doing to me?" Dean asked, unable to keep his voice from breaking which only made the Demon laugh._  
  
"I'm just giving you a better view, Baby...You are right under the surface now. You can feel, and smell and taste everything...I'm just pulling your strings so to speak. For example." The Demon leaned in and slowly slid his tongue along the rim where his fingers were pounding into the Angel's body, humming happily when he wiggled it in alongside them. Dean went silent with shock as he felt his tongue penetrate the man and he couldn't help but whimper when he tasted cum on his tongue, leftovers from his Brother's time with the Angel. "That boy really gave him an ass full am I right?" The Demon spoke in Dean's head, mouth a little busy sucking on Cas' rim and diving in to taste the Angel again. "Hmmm tastes so good like this...What do you think, Dean, you think he is wet enough to take us now?" The Demon asked and Dean wailed inside his own head as the Demon pulled his fingers out and spat into his palm, slicking up their cock before lining up with the Angel's hole. Dean prayed that the Demon would bottom out quickly and fuck his friend fast, if only so this would be over soon but with a shake of his head the Demon slowly fed Cas his cock, inch by torturous inch, until he was fully seated and Dean could no longer hold his moans. Cas' ass twitched and milked his cock, sucking it in as though desperate for everything the man could give him and when the Demon pulled back the suction was enough to set his skin alight with pleasure. When only the head of his cock was left inside the Demon placed both hands on Cas' ass and pulled his cheeks apart so he could watch as he plunged forward, shuddering at how obscene it was to watch Cas' hole stretched around his huge cock. The Angel's body opened and took him easily, and if the cries and moans from the man where anything to go by the Angel was loving every minute of it as the Demon set a punishing pace, chasing his completion. Dean was torn in two, desperate for it to end and frantic for his end...he wanted it and he didn't, and the confusion had him crying as Cas' ass swallowed up his cock and made him moan loudly into the darkened room.  
  
 _"Please stop! I'll do whatever you want but just please stop!" Dean yelled at the Demon controlling him but as he picked up the pace, skin slapping against skin as he buried himself over and over again inside Castiel, the Demon clawed at Cas' skin and marked him up easily._  
  
"But you are doing what I want Dean...I want you to fuck him. I want you to enjoy him...and you -are- enjoying him Dean, haven't you realised yet Baby?" The Demon asked with a laugh which Dean didn't understand until the awful truth washed over him like a wave.  
  
There was nothing holding him.  
  
There was no demonic power forcing his hips forward, and Dean couldn't tell for how long those thrusts had been his own, how many minutes had he been mindlessly rutting into his friends ass while he lay pasted out and helpless on the floor. Dean tried to pull back but it was too little too late, and nothing could hold back his screams as he plowed forward, buried himself as deep as he could get and came, gushing cum deep inside and filling the Angel up till it leaked out around his cock. After several minutes of clawing at Cas' back and an orgasm that seemed to last forever, Dean collapsed against the Angel's back and lay atop him, boneless and sobbing, his tears dripping onto his friend sweat soaked skin.  
  
Castiel slept on, unaware of the sin that had been done to him, and all the while the Demon laughed on inside Dean's head.  
  
"You'll never forgive yourself, Dean. Never."


	6. To Old Friends

**Summary for the Chapter:**

> Cas fucks up and pisses off the Demon, causing it to punish him and Sam once again, but it doesn't have all day to play with them...It has a meeting with a very old friend, and a familiar face to the boys, but does this old friend know more than he is letting on?

**Notes for the Chapter:**

> WARNINGS! ALL THE WARNINGS! SLAPPING, HAIR PULLING, NON CONSENSUAL BLOW JOBS, THREATS OF PHYSICAL VIOLENCE, THREATS OF GANG RAPE, SLAPPING, CHOKING, CUM MARKING...THIS IS A VERY DIRTY AND RAW CHAPTER! THERE IS MENTIONS OF PAST SEXUAL ABUSE TO ANOTHER CHARACTER BY THE DEMON AND THREATS OF FUTURE VIOLENCE AND RAPE!
> 
> DO! NOT! READ! IF! EASILY! UPSET!

When Sam came to the next morning he groaned in pain and rolled his head back, staring up at his numb arms pinned above his head. His back was alight with pain, twinges that ran all up and down his spine as he moved his head back down and looked around, finding Castiel already awake and hovering over his food bowl, eating what looked  like some kind of warm porridge. Sam watched as the Angel tucked into his food and stopped only to move over to the water bowl, lapping at the liquid with an almost expert precision. The pinned Hunter licked his dry lips and tried to call out to Cas, only to find his voice was still being silenced by the Demon's power, but when his stomach let out a loud growl Castiel's head whipped around, frightened eyes locked with his own. Both Angel and Hunter stared at one another for several minutes, and Castiel's scared eyes flitted between Sam's face and his pinned hands, but finally he seemed to deflate and he turned back to his food, ignoring the Hunter in favour of his breakfast. Sam's hurt whimper was silenced before it made it passed his lips and he ducked his head, unable to watch the Angel eat anymore as his heart started to ache. No matter how hard he tried to deny it he was breaking fast, and he didn't know how much more he could take before he was just like Castiel. The Angel might be the Demon's little bitch, but at least he was a fed bitch and he didn't spend his night pinned to a cold brick wall, forced to try and sleep on his feet while his arms slowly came alive with fiery pain. If he was completely honest with himself he knew he deserved the punishment after what he had done to Castiel, and what he had tried to do to him, but the Demon had been right - Sam was jealous. He was hurting and jealous that Cas had it easier, and that the Demon prefered Cas' company to his, as screwed up as that made him sound. He knew that the Demon was not his Brother, but it still wore Dean's face and in Sam's crumbling mind that was something that he clung on to desperatly.  
  
The door swung open and revealed the Demon, eyes pinned to Castiel who had looked up as Dean strolled in and smiled at his Master. The Angel abandoned his breakfast to crawl over to Dean, meeting him halfway across the room and butting his head against the Demon's hand as it reached down to stroke fingers through the Angel's hair.  
  
"Morning, Beautiful. Sleep well?" The Demon asked, crouching down to the Angel's level and smiling when Cas crawled closer, nuzzling his face into the Demon's chest. "I'll take that as a yes." Dean chuckled as he stroked down Cas' back, patting the Angel's butt and laughing when Cas blushed bright red and looked away embarrassed. The Demon trailed his hand around the Angel's cheeks and slowly dipped his fingers in, brushing over Cas' little hole and the Angel yelped, flinching away from the Demon's fingers. Dean's eyes went black and he growled lowly at the Angel, causing Cas to dip his body close to the floor and whimper fearfully but the Demon pulled himself back when he realised that the man wasn't trying to pull away on purpose...he was in pain. "Hurts, Baby?"  
  
"Yes, Master, a little. I'm sorry I pulled away I didn't mean to, please don't be angry with me." Castiel whimpered, keeping his eyes on the floor out of respect and missing the Demon's proud grin. It placed a hand on Cas' ass again and gave him a gentle pat, stroking over the skin.  
  
"Aw, poor Baby..." The Demon purred, helping the Angel back onto his knees. "Turn around, ass in the air. Let me see it." Dean ordered and Cas scrambled around, ducking his chest down to the floor and shuffling his knees apart, pushing his ass into the air for the Demon to see. Dean smirked and knelt behind the Angel, placing both hands on his ass cheeks and pulling them apart, running a thumb over the mans red and abused hole. Cas bit his lip to stifle his pained groan and lay his head on his arms, closing his eyes tightly, and Dean took pity on the man, leaning in close until Cas' could feel soft breath against the sensitive flesh. He felt rather than saw the Demon smile and when a hot wet tongue pushed up against the tight pucker, pointed tip wriggling its way inside, Cas had to bite down on his arm to keep from screaming in pleasure. The Demon set an incredibly slow and cruel pace as he took his time licking and kissing all around the Angel's ass, dipping his tongue inside and tasting himself from the night before, moaning at the thought. "That feel nice, Angel? You like it when I kiss you all better?"  
  
"Oh yes, Master, I like it!" Cas moaned loudly as he felt the Demon sucking at the rim and forcing his tongue back inside, all pain gone and buried under the pleasure of being eaten out. Dean pulled back and grinned at the Angel's sloppy hole, wet and glistening with his spit as it twitched and all but begged for Dean's tongue once again. The Demon slid a hand around the Angel's middle and found his cock, hard and heavy underneath him, and it gripped him tightly as it crawled over his back and whispered obscenely in his ear.  
  
"You're such a little slut, aren't you Angel?" The Demon growled lowly in Cas' ear, rutting his clothed erection against his naked ass and grinning when the Angel jerked backwards, moaning at the feeling of the Demon on his back. "You'll just bend right over and beg to have your ass filled - fingers, tongue, cock, does it even matter to you? No, you don't care as long as something is fucking you right?" Dean slid his fingers through the Angel's hair and tightened his grip, yanking his head to the side and attacking his neck with kisses and bites. The Angel cried as Dean marked him and without warning he was cumming all over the floor beneath him, shudder under the Demon and moaning when it sucked a mark onto his skin. "So fucking pretty...but tell me something...who gave you permission to cum, Bitch!" Dean growled and before Castiel could turn to beg the Demon had grabbed him by the scruff of the neck, fingers biting into his skin, and was dragging him across the room on his knees. When he reached the wall where Sam was pinned he threw the Angel down before the Hunter and smirked up at Sam.  
  
"Heya Sammy. You like getting your cock sucked right?" The Demon asked and Sam had no time to answer before Dean was dragging the sobbing Angel up onto his knees. "Yeah, course you do, everyone likes having a slut choking on their cock...Suck him, Cas." Dean ordered but the Angel shook his head and turned begging eyes on the Demon.  
  
"No please Master please no not this please he tried to..." Cas begged but Dean glared down at him and growled, hand whipping through the air and smacking the man across the jaw. The Angel squealed and put his hands over his mouth, sobbing as blood poured down his face and dripped onto the floor, but Dean was not done with him. The Demon grabbed him by the back of the neck again and forced him forward until Sam's cock - limp and uninterested - was only an inch from his quivering lips.  
  
"Get him hard Cas or I swear I'll turn you around and find something to shove up your ass...or maybe someone else..." The Demon threatened the sobbing Angel who closed his eyes tight and slowly leant forward, flicking his tongue out to lap over the Hunters soft cock. Sam groaned and turned his head away, trying to block out the sight of the Angel on his knees and the feeling of that soft little tongue on his cock but it was no good because the Demon reared up and pulled a blade out, pushing the tip up against Sam throat. "Watch him!" The Demon said in a low and deadly voice, and Sam slowly opened his eyes and stared down at the broken Angel licking at his quickly hardening cock. This went on for several minutes, Dean watching with a feral grin as Cas worked on Sam's cock, getting it hard and ready for him, his cries and whimpers falling on deaf ears as Dean undid his own jeans and pulled out his hard cock, jerking it as he watched. When Sam was finally rock hard and leaking, his hips unconsciously rutting forward and trying to force his cock head into Cas' mouth Dean withdraw his blade and leant down beside the Angel again.  
  
"I knew what he was trying to do to you, by the way. I was watching the whole time, trying to decide if I should come in and save you or watch as he tore your little ass up on his cock...and part of me wanted to see that so bad, Angel." Dean whispered to Cas as the Angel peppered Sam's cock with wet kisses, eyes wet with tears and frightened as he was forced to kiss the cock that was going to violate him once again. "I would have killed a whole host of Angels to see your hole stretched around his cock, only your blood slicking his way. It'd hurt him only for a minute but for you..." Dean whistled lowly. "It'd feel like a knife up your ass every time. Look at him, Cas..." Dean growled and Cas's eyes flicked up to meet Sam's, both filled with fear and agony as Sam shook his head, trying to make the Angel understand. "He wanted to do that to you not because I was making him do it, but because he wanted to hurt you, and if I hadn't come to your rescue he'd have raped you again and again and left you a weeping blood mess on the floor. But I saved you...And this is how you repay me?! Cumming without permission, refusing to obey my orders! You need to learn...you need to show me some respect!" Dean started yelling at the crying and frantic Angel, the grip on his neck tightening to an unbearable level as he started to force him forward again until Sam's cock was forced up against his lips.  
  
"Open up!" Dean ordered and this time Cas obeyed, opening his mouth wide and gasping when the Demon forced him forward, Sam's cock disappearing straight down his throat and forcing its way deep inside without giving Cas any time to adjust. Cas didn't even have time to breath and now he couldn't, Sam's flesh filling him up till it blocked his airway and left him fighting to fill his lungs. The Angel brought his fists up and started to hit and push at the Hunters hips while struggling frantically in the Demon's grip, trying to break away. His vision was starting to blur around the edges and he barely made out the sounds of Dean ordering Sam to fuck him as the blood pounded in his ears and made his head swim. As he reached the brink of unconsciousness the Demon pulled him back, giving him a chance to pull in a quick breath before he forced him forward again and held him still, waiting till the Angel was frantic again before repeating the process. Every time got harder and harder to stay alert and after a few times Dean yanked him off and slapped him repeatedly around the face to liven him up, ignoring his cries and pleas for mercy. Once the Angel was forced back onto Sam's cock the Demon turned its black eyes on the Hunter pinned to the wall and grinned at the sight of his little Brother watching Castiel choke with tears in his eyes.  
  
"Aw whats the matter, Sammy? I thought this was what you wanted?" The Demon asked and Sam shook his head but his response was rendered moot when Cas' throat spasmed around his cock and made him moan aloud, hips thrusting forward and forcing his cock deeper. "Oh but it was Sammy, you can't lie to me you wanted to hurt him. You wanted to fuck him and feel him struggle on your cock, you didn't care if he cried you liked seeing him hurting...go on, baby Brother, fuck him. Rape his face, I'll hold him down for you." The Demon said, his voice like silk and Sam shook his head, trying to ignore the pulling in his belly that warned him he was about to cum. He was trying to hard to fight it but the feeling of Cas around his cock was too good, and it didn't matter if the Angel was willing or not, all that mattered was that the squirming and whimpering little Bitch stayed put while he ruined his throat.  
  
"Sammy!" Dean barked and Sam jumped in fear, his eyes darting between Dean and the Angel on his knees who was fast turning blue from lack of oxygen. "You give this little cunt a mouthful of cum or I will find a horde of Demons will to fill him up for you! I'll even let you watch them, wouldn't that be nice?" Sam's eyes went wide and he started to frantically thrust forward, only managing a handful of times before he blew his load, pumping cum down Cas' throat and crying out frantically, partly from pleasure and partly from fear...Cas had went limp in Dean's grip and his struggling had ceased...he didn't even choke when Sam's cum shot down his throat. Dean let go of the Angel's neck and allowed him to drop to the floor, ignoring Sam's frantic cries as he rolled Cas onto his back and started to jerk his cock, working himself up until he came with a grunt all over the Angel's face, grinning when some of it landed in his lax mouth. As the Demon came down he rolled Cas onto his side and leant down, whacking him three times on the back until the Angel came to, choking and gasping for air as the world came back into focus. Dean ignored both the men, and straighted his clothes, tucking his cock back inside his pants as Sam cried and struggled against his bonds, trying to make it to Cas who was curled up and shaking on the floor, cum staining his face and leaking from his mouth.  
  
"Such a shame I was hoping to have a good day today...well, I had fun but I was hoping you two would be better behaved. Oh well, we have plenty of time and training left to go and until then we always have your punishments to look forward to..." Dean grinned at the thought of all the wonderful ways he could hurt his little pets and he snapped his fingers, laughing when Sam's restraints suddenly came loose and the man crashed to the floor beside Castiel. "Opps. Sorry, little warning next time. Now I am sure you two have a lot to talk about so I am gonna leave you alone. Daddy has a very important meeting to go to and I can't stick around here playing with you all day, much as I'd love to. But I promise I'll be back later to check on you...and I hope you to are feeling a little more grateful when I do." Dean said, winking at the two cowering figures and walking out the door, slamming it shut behind him, the sound of the bolt sliding home the only sound apart from Castiel's broken sobs.  
  
  
\----------  
  
  
The Demon was feeling a lot more refreshed when he made his way upstairs to the small room that he had taken as his Office Space. Since his escape from Hell and his taking of his delicious vessel he had found that many of the lower Demons had begun to look to him as a leader, and it was causing a bit of a power shift in Hell - which was the reason for the meeting he had set up for this morning. Crowley was supposed to be here around eleven and he had been hoping to bring Castiel upstairs to keep him company while he listened to the Crossroads Demon babble on about the politics of Hell. It was going to be extremely boring and he had hoped to occupy himself with the Angel's hot little mouth around his cock but it would seem that they were both still too untrained to be allowed upstairs with him. Soon though...  
  
The Demon was smiling to himself when Crowley's engery announced itself and he waited a moment before willing the door open, standing up and walking around the desk to greet the lower level Demon as it walked into the office with a smile.  
  
"Fergus!" The Demon said with a grin, pulling the smart dressed little Demon into a hug and patting his back.  
  
"Actually, its Crowley now." Crowley corrected, returning the embrace and rolling his eyes when the Demon cupped his face and patted his cheek, searching his face.  
  
"I know, I heard! King of Hell, huh? I always knew you'd go far, my prodigy...I am so proud of you." The Demon's eyes flicked black and Crowley's hazed over in red, the pair playfully sizing the other up in a way only Brothers could understand. When the Demon turned and walked back to his seat, motioning for Crowley to take his own across from him the Crossroads Demon began to talk.  
  
"Actually, before I sit there is just one thing..." Crowley said and the Demon raised an eyebrow curiously, his expression shifting to happiness when Crowley pulled a bottle of fine Scotch and two tumblers from thin air. He placed both glasses on the desk and poured a healthy shot into each of them, presenting on to the Demon and lifting his own in salute. "To your Grand Resurrection." The Crossroads Demon toasted and the Demon raised his own glass before downing it on one shot and placing the glass back on the table. The Demon snagged the bottle and poured another two shots, raising his glass to Crowley with a smile.  
  
"To our new found partnership." The Demon toasted and Crowley raised his glass respectfully, downing the second shot and placing his glass down. "Well now that the pleasantries are out of the way how about we get down to business, we got a lot to discuss if we are going to be ruling Hell together." The Demon said, leaning back in his chair and kicking his feet up on to the desk, while Crowley clasped his hands in his lap and smiled at him, nodding politely along as the Demon ranted on about his plans to revamp Hell and how by the end of the year they would be running at full capacity once again. "I mean no offense to you and how you run things now, but you can't tell me you actually enjoy all this 'Lets Make A Deal' crap! I mean who the Hell does that anymore? These Humans are ours for the taking, and we shouldn't have to justify our actions, am I right?" The Demon said, downing yet another glass of Scotch and motioning for Crowley to pour him another, which the Crossroads Demon did with a nod.  
  
"I couldn't agree more, my Lord! And we are so looking forward to your first visit down to the pit. I should love to show you around personally and you can tell me exactly what it is you would like changed, I am at your service." Crowley simpered, and the Demon smiled proudly at his child as he took the offered drink from him.  
  
"I knew I could count on you, Fergus. You always were my best student...my personal favourite..." The Demon said, its eyes roaming up and down Crowley's demonic form and its tongue darting out to wet its lips obscenely. Crowley turned his face away and for a moment the younger Demon looked nervous but the Demon started to laugh and reached over to slap Crowley on the shoulder. "Oh would you relax a little, Fergus! You know I don't go back once I grow bored of you...although you my little one were a hard ass to leave. But! I have other pleasurable arrangements to work with now...I think you know them, a Sam Winchester and the Angel Castiel?" The Demon smirked when Crowley's head snapped up to look at him, shock written all over his features but he covered it quickly, smiling at his old Master.  
  
"Yes, I have had the pleasure of working with both of them. A word of warning, be wary of that Sam he is a slippery character and not afraid of bending the rules to get what he wants." Crowley said, taking a deep drink straight from the Scotch bottle.  
  
"Noted, although I have found that its the Angel who is the most slippery of all...more so when my wicked tongue is stuck up his ass." The Demon said and barked with laughter when Crowley choked on his drink, spitting it all over the desk as he coughed and spluttered. Crowley gripped the desk and tried to get his breathing back under control as the Demon walked around behind him and patted him on the back, fingers settling on the back of his neck and sending a chill through his vessel. "You never could handle your liquor could you? I remember you used to get so drunk you'd be like putty in my hands, all limp and helpless...why'd you get rid of that boys vessel, it suited you so well?" The Demon asked as he smirked down at his nervous friend.  
  
"...It didn't feel right to keep it around after you disappeared..." Crowley muttered, flinching slightly when the Demon pulled his hand away and leant down beside him, putting his lips to the little Demon's ear.  
  
"Well it is lucky for you that I have no interested in seeing you in it once again...although I could easily do it if I should ever find out that you were slinking around behind my back. Do I make myself clear?" The Demon threatened in a voice light but menacing and Crowley gulped nervous, nodding with a small smile.  
  
"I'm no snake, my Lord. I'd never cross you, you know that." Crowley said, locking eyes with the Demon and holding his gaze until a proper smile graced his lips and he stood up, placing a hand on Crowley's shoulder.  
  
"Good. I would hate to have to put you in your place again after I worked so hard to train you." And with that the Demon was gone, walking away from Crowley and back to his seat without a backward glance. "You can show yourself out and call me later in the week to set up a walk-through of Hell. Your dismissed." The Demon said but before Crowley could stand it had looked up again. "Oh wait, you are staying close by aren't you? I hardly believe you are rooming in Hell these days..."  
  
"Oh yes, I am staying in an apartment not too far away from here..." Crowley confirmed, getting to his feet and slowly making his way to the door.  
  
"How is the nightlife around here? Worth heading out for a drink?" The Demon asked and Crowley looked back at him, one hand on the doorknob, but he was no longer seeing the Demon. He was looking through the vessel, past the darkness and into the small struggling soul inside him.  
  
"Oh yes. Its a really Funkytown."


End file.
